1-(3,4-dimethylphenyl)-3-nitro-1H-pyrazole → HCID 28301245, compound

HRID 926854Notes

Reaction equation

HRID 926854 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]>CO.C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 1

HCID 665875041-(3,4-dimethylphenyl)-3-nitro-1H-pyrazole

Product 1

HCID 28301245HCID 28301245, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Into a 100-mL round bottom flask, was placed a solution of 1-(3,4-dimethylphenyl)-3-nitro-1H-pyrazole (900 mg, 4.15 mmol, 1.00 equiv) in methanol/ethyl acetate (20/10 mL). The solution was treated with Pd/C (500 mg) and stirred under an atmosphere of hydrogen overnight at room temperature. The reaction progress was monitored by LCMS. The solids were filtered out. The resulting mixture was concentrated under vacuum to yield 750 mg (97%) of 1-(3,4-dimethylphenyl)-1H-pyrazol-3-amine as a yellow solid.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-e9fee79c56734419b4d2f9ad3c0837ad
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

Loading…